This 2 hour sailing excursion may take place in Pensacola Bay, passing by areas of Sabine Island, Deer Point, Fair Point and Deadman's Island. We may also sail east under the Bob Sikes (Pensacola Beach) Bridge, exploring areas of Quietwater Beach and the Santa Rosa Sound. A small group atmosphere makes this tour so enjoyable. The Jolly Mon can accommodate parties of up to 6 guests maximum. Sailing is a unique experience and fun for all ages. This tour is great for families, couples, adventurers and seekers of relaxation alike! Guests can learn from the Captain about the area wildlife, history, and the art of sailing. Take the helm and learn to sail or just sit back and enjoy the sights and sounds. Once we leave the dock and motor through the channel, we set sail for a tranquil excursion. There is something special about traveling across the water with only the power of the wind. Every tour is different, but always such a fun and easygoing activity, so many lasting memories to be made!

• Avoid the hassle of driving between tastings
• Hassle-free transfers from downtown Yountville
• Learn about the winemaking process
• A private tour means a personalized experience

What To Expect

Sailing in Pensacola has been a tradition since 1559, when Don Tristan De Luna of Spain
landed on the shores of Pensacola Bay, marking the first European settlement in mainland America.
The tradition continues today, as the area is training headquarters for the New York Yacht
Club America's Cup team sailing vessel, American Magic.

On the Jollymon, our sporty custom 27’ American
Mariner sailboat, you can experience a sailing adventure just like the early explorers. Your Captain
will be happy to show you the ropes, and even let you steer the boat,
if you feel adventurous!

Sailing is a wonderful experience that is relaxing and exciting at
the same time.
Sit back, relax and enjoy the scenery, along with a cold beverage or
two! Complimentary beverages, including beer and wine, are offered on this cruise for guests of
legal drinking age.

Sailing with dolphins on Northwest Florida’s Gulf Coast is a unique experience.
Wild dolphins seem naturally attracted to sailboats, often swimming alongside us, crossing our wake, playing
and feeding nearby. Though we cannot always guarantee a sighting, we do cross paths with
dolphins and other sealife often on sailing excursions.